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Cesium carbonate → 4-Chloro-2-(difluoromethyl)-1-(2-{[4-(methylsulfonyl)phenyl]oxy}ethyl)-1H-indole-5-carbonitrile

HRID 2101859
Notes
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Reaction equation

HRID 2101859 reaction equation
[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:13]([F:15])[F:14])[NH:6]2.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH2:33][CH2:34]Br)=[CH:28][CH:27]=1)(=[O:25])=[O:24]>CC#N>[Cl:1][C:2]1[C:10]([C:11]#[N:12])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH:13]([F:14])[F:15])[N:6]2[CH2:34][CH2:33][O:32][C:29]1[CH:28]=[CH:27][C:26]([S:23]([CH3:22])(=[O:25])=[O:24])=[CH:31][CH:30]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 249856324-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrileHCID 438069541-(2-Bromoethoxy)-4-methanesulfonylbenzene

Product 1

HCID 249861264-Chloro-2-(difluoromethyl)-1-(2-{[4-(methylsulfonyl)phenyl]oxy}ethyl)-1H-indole-5-carbonitrileYield 61.6%

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-chloro-2-(difluoromethyl)-1H-indole-5-carbonitrile (0.019 g, 0.084 mmol) in MeCN (2 mL), under N2, was added Cs2CO3 (0.055 g, 0.17 mmol) and 4-[(2-bromoethyl)oxy]phenyl methyl sulfone (0.047 g, 0.17 mmol). The mixture was heated in a sealed tube at 100° C. for 1 h. Upon cooling, the mixture was partitioned between EtOAc and water. The organic phase was washed with sat'd brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography (0-70% EtOAc-hexanes gradient) and the product was crystallized from CH2Cl2-hexanes to give the title compound as a white solid (0.022 g, 61% yield): MS (ES) m/z 425 (M+1).

Workup

  1. temperatureUpon cooling
  2. customthe mixture was partitioned between EtOAc and water
  3. washThe organic phase was washed with sat'd brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (0-70% EtOAc-hexanes gradient)
  7. customthe product was crystallized from CH2Cl2-hexanes

Sources & evidence

ORD record
ord-61b7ac8cfddb48878c4a4a9023e3ceeb
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07572820B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes